Dimethylformamide → 6-chloro-N-[5-(3-dimethylaminobenzamido)-2-methylphenyl]pyridine-3-carboxamide

HRID 2302238Notes

Reaction equation

HRID 2302238 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8](Cl)=[O:9])=[CH:4][CH:3]=1.[NH2:11][C:12]1[CH:13]=[C:14]([NH:19][C:20](=[O:30])[C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([N:27]([CH3:29])[CH3:28])[CH:22]=2)[CH:15]=[CH:16][C:17]=1[CH3:18].C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O.C(Cl)Cl>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([NH:11][C:12]2[CH:13]=[C:14]([NH:19][C:20](=[O:30])[C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([N:27]([CH3:28])[CH3:29])[CH:22]=3)[CH:15]=[CH:16][C:17]=2[CH3:18])=[O:9])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 27821656-Chloronicotinoyl ChlorideHCID 22057981HCID 22057981, compound

Product 1

HCID 98661856-chloro-N-[5-(3-dimethylaminobenzamido)-2-methylphenyl]pyridine-3-carboxamideYield 14.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

6-Chloropyrid-3-ylcarbonyl chloride (0.37 g) was added to a mixture of N-(3-amino4-methylphenyl)-3-dimethylaminobenzamide (0.54 g), potassium carbonate (0.304 g), DMF (5 ml) and methylene chloride (20 ml) and the resultant mixture was stirred at ambient temperature for 16 hours. The mixture was poured into water and extracted with ethyl acetate. The organic extracts were washed with a saturated aqueous sodium chloride solution, dried over magnesium sulphate and evaporated. The residue was purified by column chromatography on silica using a 3:2:1 mixture of isohexane, ethyl acetate and methylene chloride as eluent. There was thus obtained the title compound as a solid (0.122 g); NMR Spectrum: (DMSOd6) 2.19 (s, 6H), 3.28 (s, 3H), 6.88 (m, 1H), 7.25 (m, 4H), 7.57 (m, 1H), 7.7 (d, 1H), 7.84 (d, 1H), 8.36 (m, 1H), 8.95 (d,1H), 10.11 (s, 1H), 10.16 (s, 1H); Mass Spectrum: M+H+ 409 and 411.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic extracts were washed with a saturated aqueous sodium chloride solution
  3. dry with materialdried over magnesium sulphate
  4. customevaporated
  5. customThe residue was purified by column chromatography on silica using
  6. additiona 3:2:1 mixture of isohexane, ethyl acetate and methylene chloride as eluent

Sources & evidence

ORD record
ord-48035327f0504d319f58fde8c1c65fa6
Source dataset
uspto-grants-2002_08
Patent number
US06432949B1

Reaction notes

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